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The Gemara Brachot (20b) states that the mitzvah of Kiddush is a Torah obligation derived from the pasuk: "Zachor et Yom HaShabbat L'kadsho". However, the nature of the mitzvah ofHavdala is unclear. The Rambam (Hilchot Shabbat 29:1) writes that Havdala is also a mitzvah from the Torah, derived from the very same pasuk. Kiddush and Havdala are two parts of the same mitzvah. The Maggid Mishneh comments that there are those who disagree with the Rambam and claim that Havdala is a Rabbinic obligation.

Even according to the Rambam, the Torah obligation of Kiddush and Havdala involves only the recitation of certain ideas. The need to say these brachotover a cup of wine is mandated by Rabbinic decree. (Hilchot Shabbat, 29:1, 6) The Gemara Brachot (33a) relates that originally, the Sages legislated that the mitzvah of Havdala may be performed through davening. Later when the economic status of the Jews improved, it became mandatory to recite Havdala on a cup of wine. Much later, when there was an economic decline, Chazal legislated that Havdala should again be said during davening, but must also be said over wine.

With this background in mind, let us examine the question of saying Havdala when Tish'a B'av occurs on Motza'ai Shabbat. The problem is self-evident: one is required to recite Havdala on Saturday night on a cup of wine. Someone must drink the wine. It is Tish'a B'av and we are prohibited from drinking or eating. The Rosh(Taanit 4:40) cites four possible solutions to the problem:

1. The Gemara Brachot (27b) permits one to recite Havdala on Shabbat afternoon before sunset (after Plag HaMincha). The BH”G (Baal Halachot Gedolot) raises the possibility that a person will recite Havdala before sunset on Shabbat and drink the wine. (Of course, one is still prohibited from performing melacha until nightfall.) This opinion is rejected because the moment he recites Havdala, it is equivalent to accepting the fast, and he is prohibited from drinking the wine. 2. A second possibility suggested by theBH”Gis to recite Havdalaon Sunday night after the fast is over. Even according to the opinion in the Gemara that Havdala cannot be said after nightfall on Sunday, here it is allowed since it could not have been said earlier. This approach also met with some objection. One who is required to recite Havdala on Motza'ai Shabbat, but wasn't able to, can recite it as late as Tuesday afternoon (according to the more lenient opinion). However, if one wasn't obligated to say Havdala when Shabbat ends, there is no need (and no permission) to recite it later in the week. 3. The third possibility suggested by the Ramban, is to skip Havdala on wine. The Gemara mentioned earlier that Havdala was instituted over wine when the Jews became wealthier. On Tish'a B'av all Jews are considered poor and downtrodden, and therefore, there is no need to say Havdala on wine. 4. The fourth suggestion is to recite Havdala on Saturday night and give the wine to a minor to drink. Even though the Gemara Eruvin (40b) rejects this possibility for Kiddush on Yom Kippur, here we are dealing with a Rabbinic fast day, and a situation which is not a normal occurrence (Tish'a B'av on Saturday night).

What is the halacha? The Shulchan Aruch (O.C. 556:1) writes that one recites Havdala on Sunday night after the fast. The bracha on fire is said on Saturday night. There is no requirement to say the brachaon spices. (Normally the spices are meant to provide some pleasure to the soul. On Tish'a B'av we are supposed to be sad.) On Saturday night, of course one should recite the Havdala prayer in the Maariv Shmoneh Esrei ("Atah Chonantanu") or at least say Baruch Hamavdil Ben Kodesh L'chol before performing any melacha.

What should a person do if he is ill and is required to eat on Tish'a B’av? Since a person is prohibited from eating after the conclusion of Shabbat until he recites Havdala on wine, he must say Havdala. However, it is preferable for him to use one of the permissible beverage alternatives to wine, or give the wine to a youngster to drink. If neither is possible, he may drink the wine himself, but should limit himself to the minimum necessary. (See Shmirat Shabbat K'hilchata 62:46).

If a woman needs to eat, the situation is a little more complicated. There is a disagreement amongst the Rishonim whether women are obligated in Havdala (similar to Kiddush) or whether they are exempt from the mitzvah (since it is a mitzvat aseh she'hazman grama.) The Rama (O.C., 296:8) writes that, consequently, women should not recite Havdala themselves; rather they should hear it from a man. The Mishna Brurah quotes the Bach and Magen Avraham who disagree. Ashkenazic custom is that women are allowed to recite the bracha on a mitzvah from which they are exempt. Havdala is no exception.

In our situation, since there are those who say a woman should not say Havdala on her own (and there is an added factor here, that, according to some Rishonim, there is no need at all for Havdala when Tish'a B'av is on Sunday) it's preferable that a man recite Havdala for the sick woman, and she should drink the beverage (or give the wine to a minor). He will, at that time, fulfill his own obligation to say Havdala and has no need to repeat it after the fast. If there is no adult male available, the woman may recite Havdala herself. (Shmirat ShabbatK’hilchata 62:48)

May we soon merit the prophecy of Zecharya (8:19) that the fasts of Tammuz, Av, Tishrei, and Tevet will become days of "Sasson, Simcha, u'Moadim Tovim".